Both The Curse of Chalion and its sequel Paladin of Souls (2003) are set in the landlocked medieval kingdom of Chalion. The Hallowed Hunt (2005) is a novel that takes place in the Weald to the south of Chalion and two to three hundred years earlier.

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Lupe dy Cazaril, a castillar (a knight or minor baron), returns home to the Royacy (Kingdom) of Chalion a broken man, though he is only in his mid-thirties. "Caz", as he is known to his friends, had defended a castle during a long siege, only to be ordered to surrender it. Afterward, a jealous enemy had seen to it that he was not ransomed (as were the rest of his men), but sold into slavery, spending 19 months as a galley slave before finally escaping.

His old noble patroness finds a use for him as a tutor for her granddaughter, the Royesse (Princess) Iselle, half-sister to the king, and her companion, Lady Betriz. Despite his ardent desire to live a safely low-profile, peaceful life, Caz finds himself drawn into a strange journey of dangers both spiritual and temporal as he seeks to dispel the debilitating curse that hangs over the royal family of Chalion.

Chalion is a looking-glass version of the kingdom of Castile and León, and the novel is loosely based on the lives of Isabella I of Castile and Ferdinand II of Aragon, the unifiers of Spain.[2] However, the story of The Curse of Chalion is not simply a retelling of the lives of Isabella and Ferdinand, and Chalion is not simply Castile. The story takes quite a different path from the historical one, and the major characters are distinct personalities, not simply versions of historical people.